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Synthesis, biological evaluation and SAR analysis of novel poly‐heterocyclic compounds containing pyridylpyrazole group
Author(s) -
Wang BaoLei,
Zhu HongWei,
Li ZhengMing,
Wang LiZhong,
Zhang Xiao,
Xiong LiXia,
Song HaiBin
Publication year - 2018
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.4770
Subject(s) - mythimna separata , alternaria , stereochemistry , chemistry , fungicide , bioassay , alternaria solani , anthranilic acid , proton nmr , mode of action , organic chemistry , biology , botany , biochemistry , lepidoptera genitalia , genetics
BACKGROUND In recent years, pyridylpyrazole derivatives, such as pyridylpyrazole‐containing anthranilic diamide have attracted much attention by virtue of their useful insecticidal properties and unique action mode. Moreover, some pyridylpyrazole‐containing compounds have also been found to possess significant fungicidal activities. With the aim of discovering new bioactive agrochemicals for crop protection, a series of poly‐heterocyclic compounds containing pyridylpyrazole and aziridine, or β‐lactam, or thiazolinone moieties were synthesized. RESULTS A series of pyridylpyrazole‐containing poly‐heterocyclic compounds were obtained, and confirmed through IR, 1 H NMR, 13 C NMR, HRMS and elemental analysis. The crystalline structure of 4‐(3‐bromo‐1‐(3‐chloropyridin‐2‐yl)‐1 H ‐pyrazol‐5‐yl)‐3‐chloro‐1‐mesitylazetidin‐2‐one (compound 13f ) was determined to further illustrate a trans‐ configuration of the β‐lactam motif. In addition, bioassays showed that most of these new compounds exhibited modest insecticidal activity towards Mythimna separate Walker at 200 µg mL −1 . Some of the compounds displayed excellent fungicidal activity towards some plant fungi, including Cercospora arachidicola ( 13j : EC 50 = 14.5 µg mL −1 ), Physalospora piricola ( 12d and 13d : EC 50 = 10.5 and 9.70 µg mL −1 ), Alternaria solani Sorauer ( 13j : EC 50 = 7.29 µg mL −1 ) , Puccinia sorghi Schw. ( 13d : control efficacy 99.0 ± 2.1% at 200 µg mL −1 ) and Erysiphe graminis ( 14d : control efficacy 95.0 ± 1.4% at 200 µg mL −1 ). CONCLUSION Compounds 12b – 12e , 13a , 13d , 13f , 13j , 13 k and 14d could be considered potential fungicidal lead compounds to do further structural optimization. The structure–activity relationship analysis in this study brings some new understanding to the biological activities of N ‐pyridylpyrazole‐containing compounds, and provides important information for the research and development of novel agricultural fungicides with poly‐heterocyclic structures. © 2017 Society of Chemical Industry